HCID 13417979, compound → 2,3-Dihydro-2-(2,2-diethoxyethyl)-3-(1-aminoethyl)-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of the two isomers of 2,3-dihydro-2-(2,2-diethoxyethyl)-3-(1-nitroethyl)-isoindol-1-one (2.5 g, described in Example 30) and 10% palladium on carbon (0.25 g) in acetic acid-water (4:1, 50 ml) is stirred under an atmosphere of hydrogen at 50 psi and 25° C. for 18 hr and filtered. The filtrate is evaporated and dissolved in 2% hydrochloric acid. The solution is washed with diethyl ether, basified to pH 9 with ammonium hydroxide and extracted with ethyl acetate. The organic extract is dried, evaporated and chromatographed on silica gel using acetone-benzene (2:3). Evaporation of the eluates gives isomer A (1.14 g) of the title compound, ir (CHCl3) 1675, 1120 and 1050 cm-1 and isomer B (0.88 g) of the title compound, ir (CHCl3) 1675, 1120 and 1050 cm-1.

Provenance & Evidence